4-Hydroxybenzaldehyde → 4-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

HRID 1828829Notes

Reaction equation

HRID 1828829 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1>ClCCl>[C:10]([Si:14]([CH3:16])([CH3:15])[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehydeYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Hydroxybenzaldehyde (5.14 g, 42.1 mmol) was added to a suspension of tert-butyl-dimethyl-silyl chloride (6.7 g, 44.4 mmol) and imidazole (3.03 g, 44.5 mmol) in dichloromethane (100 ml) under an atmosphere of nitrogen at room temperature. The reaction mixture was stirred at room temperature for 18 hours, and then washed sequentially with 1 M hydrochloric acid (2-fold 50 ml) followed by a saturated aqueous solution of sodium hydrogen carbonate (50 ml). The organic phase was separated, dried over anhydrous magnesium sulphate and the solvent removed in vacuo. The residual yellow oil was passed through a plug of silica gel eluting with 1:1, by volume, dichloromethane:pentane giving 4-(tert-butyl-dimethyl-silanyloxy)-benzaldehyde (7.5 g) as a golden yellow oil.

Workup

  1. washwashed sequentially with 1 M hydrochloric acid (2-fold 50 ml)
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e87d531af4394fddbe5f9f1b922e4743
Source dataset
uspto-grants-2006_06
Patent number
US07060717B2

Reaction notes

Loading…